US3220971A - Polyethylene containing dioctyl phosphate or octyldiphenyl phosphate - Google Patents

Polyethylene containing dioctyl phosphate or octyldiphenyl phosphate Download PDF

Info

Publication number
US3220971A
US3220971A US141583A US14158361A US3220971A US 3220971 A US3220971 A US 3220971A US 141583 A US141583 A US 141583A US 14158361 A US14158361 A US 14158361A US 3220971 A US3220971 A US 3220971A
Authority
US
United States
Prior art keywords
phosphate
polyethylene
composition
octyldiphenyl
polyethylene containing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US141583A
Other languages
English (en)
Inventor
Barillet Francis
Genier Marie
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kuhlmann SA
Original Assignee
Kuhlmann SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kuhlmann SA filed Critical Kuhlmann SA
Application granted granted Critical
Publication of US3220971A publication Critical patent/US3220971A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds

Definitions

  • This invention relates to the preparation of odorless ethylene polymer and copolymer products.
  • An object is to control the formation of persistent odor-generating by-products during the manufacturing process of polyethylene and ethylenecopolymer articles.
  • the invention is based on the unexpected discovery that the incorporation of organic phosphates, in the polyethylene or ethylene copolymer compositions, will prevent the formation of odor-generating by products even where the composition contains residual metallic compounds, anti-oxidizers and the like.
  • polyethylene will be used to include, where applicable, both polymers of ethylene and copolymers of ethylene with other compounds.
  • the invention accordingly comprises the method of producing substantially odorless polyethylene products, which method is characterized by the step of including a small proportion of one or more organic phosphates in the polyethylene composition.
  • the invention likewise includes the polyethylene products and shaped articles produced by the specified method.
  • the addition of organic phosphate is made prior to the addition of anti-oxidant or other stabilizer agents into the composition.
  • the stabilizer agent if soluble, is dissolved or otherwise dispersed in a selected liquid organic phosphate, and the solution or dispersion is added to the polyethylene composition.
  • a suitable compatible solvent may be added to a mixture of organic phosphate and stabilizer, and the resulting solution added to the polyethylene.
  • the auxiliary solvent may, if desired, be selected sulficiently volatile for ready elimination thereof from the composition.
  • organic phosphates including both neutral and acidic salts, may be used according to the invention.
  • the phosphates should be selected from within the group of innocuous organic phosphates approved by the competent sanitary agencies.
  • an organic phosphate usable according to the invention is octyldiphenyl-phosphate.
  • the organic phosphates may be incorporated in the composition in a wide range of proportions for the purposes of the invention. Preferably the proportion is in the range of from 0.002% to 1% by weight of the polyethylene.
  • the organic phosphate may be added to the molten polymer, e.g., within a temperature range from 150 to 200 C. by any suitable mechanical or other means, e.g., in a ribbon machine, a roller mill, an internal mixer, or otherwise.
  • the phosphates form into complexes with any metal compounds present in the polyethylene composition, and thereby prevent subsequent reaction of said compounds with the polymer and/or the stabilizer and/ or anti-oxidizer agent, even under the high-temperature conditions encountered during the shaping stage.
  • Example I A polyethylene composition was prepared by a conventional process with chromium oxide on silica-aluminia carried as a catalyst. The catalyst was retained in the polymer composition, in an amount representing about 0.2% by weight of the polymer. To grams of the polyethylene composition there was incorporated 0.1 g. of the anti-oxidant sold as Ionol (2,6-ditert-butyl-4- methyl-phenol), using a roller mill at C. The resulting stabilized polymer composition was ground and moulded into plates in a molding press in which the press pot was heated to about 250 C.
  • the anti-oxidant sold as Ionol (2,6-ditert-butyl-4- methyl-phenol
  • the resulting plates had a disagreeable odor which persisted for many weeks, especially when stored in a confined space.
  • Example 11 A polyethylene composition was similarly prepared with chromium oxide on silica-alumina as a catalyst. The catalyst was retained in the composition, in an amount of about 0.2% by weight of the polymer. To 100 grams of the composition there was then incorporated according to the invention 0.25 g. octyldiphenylphosphate, using a roller mill at 150 C. Thereafter 0.1 grams of Ionol anti-oxidant were incorporated by the same procedure. The resulting polymer composition was ground and moulded into plates by the same procedure as in Example I.
  • the plates were found not to possess any perceptible smell even when stored in confined conditions.
  • Example III In an internal mixer operated at a temperature of 150 C. 0.5 g. octyldiphenylphosphate was incorporated in 100 g. of an ethylene-butene-l copolymer containing 0.5 g. chromium oxide on silica-alumina as a catalyst. 0.1 g. of Ionol antioxidant was then incorporated in the mix. Plates were moulded from the composition as above, and were found to be completely odorless even under confined conditions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
US141583A 1961-03-22 1961-09-29 Polyethylene containing dioctyl phosphate or octyldiphenyl phosphate Expired - Lifetime US3220971A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR856501A FR1292337A (fr) 1961-03-22 1961-03-22 Procédé d'obtention de polyéthylène inodore et produit ainsi obtenu

Publications (1)

Publication Number Publication Date
US3220971A true US3220971A (en) 1965-11-30

Family

ID=8751462

Family Applications (1)

Application Number Title Priority Date Filing Date
US141583A Expired - Lifetime US3220971A (en) 1961-03-22 1961-09-29 Polyethylene containing dioctyl phosphate or octyldiphenyl phosphate

Country Status (3)

Country Link
US (1) US3220971A (fr)
FR (1) FR1292337A (fr)
GB (1) GB986197A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5473842A (en) * 1977-11-25 1979-06-13 Mitsubishi Petrochem Co Ltd Polyolefin resin composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2825721A (en) * 1953-01-27 1958-03-04 Phillips Petroleum Co Polymers and production thereof
US2952658A (en) * 1955-12-19 1960-09-13 Dow Chemical Co Linear polyethylene stabilized with alkali phosphates
US2980964A (en) * 1956-01-14 1961-04-25 Distillers Co Yeast Ltd Linear polyethylene films of improved transparency and method of making same
US2985617A (en) * 1955-09-02 1961-05-23 Monsanto Chemicals Stabilized polymer of 2 to 3 carbon atoms
US3020258A (en) * 1959-08-31 1962-02-06 Phillips Petroleum Co Odor inhibitors for olefin polymers

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2825721A (en) * 1953-01-27 1958-03-04 Phillips Petroleum Co Polymers and production thereof
US2985617A (en) * 1955-09-02 1961-05-23 Monsanto Chemicals Stabilized polymer of 2 to 3 carbon atoms
US2952658A (en) * 1955-12-19 1960-09-13 Dow Chemical Co Linear polyethylene stabilized with alkali phosphates
US2980964A (en) * 1956-01-14 1961-04-25 Distillers Co Yeast Ltd Linear polyethylene films of improved transparency and method of making same
US3020258A (en) * 1959-08-31 1962-02-06 Phillips Petroleum Co Odor inhibitors for olefin polymers

Also Published As

Publication number Publication date
GB986197A (en) 1965-03-17
FR1292337A (fr) 1962-05-04

Similar Documents

Publication Publication Date Title
US4504615A (en) Treating polymers of ethylene
US2419354A (en) Preservation of synthetic rubber
US3745145A (en) Stabilized melt-processable ethylene/chlorotrifluoroethylene copolymer compositions
US3220971A (en) Polyethylene containing dioctyl phosphate or octyldiphenyl phosphate
US2296363A (en) Deterioration retarder
US2956978A (en) Polyalkylene glycol dibenzoates, process of making same and resinous compositions plasticized therewith
KR102261508B1 (ko) 락테이트계 화합물이 첨가된 상온 복합분해 첨가제 조성물 및 이로부터 제조되는 사출용 펠렛
US2921917A (en) Powdery stabilizer compositions for vinyl chloride resins, and method of preparation
US3397162A (en) Non-blocking water-soluble polyvinyl alcohol films
US2967852A (en) Low pressure polyolefine with a phosphoric acid salt stabilizer
US3527730A (en) Stabilization of polymers with alkali and alkaline earth metal salts
US3549587A (en) Stabilisation of polymers
US2435853A (en) Compounding butadiene-acrylonitrile copolymer with an alcohol ester of a mono-alkenyl substituted succinic acid
US3068193A (en) Esters of epoxy fatty acids and 2, 4-dihydroxy benzophenone
US2100085A (en) Production of vulcanized rubber
US3239481A (en) Novel elastomeric compositions
US3344125A (en) Process for crosslinking a saturated synthetic rubber using a sulfur liberating material and an organic peroxide
JPH0469657B2 (fr)
US2968630A (en) Rubber antioxidant and method of preparation
US3554964A (en) Stabilization systems for polymers
US3201368A (en) Polyolefins stabilized with an (alkylphenol) monosulphide and a nickel alkoxide
US2473016A (en) Method of reducing cut-growth rate of rubberlike butadienestyrene copolymer
JPS63286459A (ja) 樹脂組成物
CN115819980B (zh) 一种环保阻燃泡沫硅橡胶及其制备方法和应用
US3361729A (en) Polypropylene composition